


The Big Night

by A_Diamond



Series: SPN Kink Bingo 2017 [6]
Category: Supernatural
Genre: Alternate Universe - High School, Anal Fingering, Anal Sex, Blow Jobs, First Time, Fluff, Insecurity, Light Angst, Loss of Virginity, M/M, Not Underage, Virgin Castiel, Virginity
Language: English
Status: Completed
Published: 2017-10-08
Updated: 2017-10-08
Packaged: 2019-01-10 21:40:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,806
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12308346
Author URL: https://archiveofourown.org/users/A_Diamond/pseuds/A_Diamond
Summary: “Maybe we shouldn’t,” Dean says at the worst possible time.





	The Big Night

**Author's Note:**

> SPN Kink Bingo square: Virginity. Masterpost [here](http://alxdiamond.tumblr.com/kink).

“Maybe we shouldn’t,” Dean says at the worst possible time.

Hunched over on the still-nearly-made bed with one finger worked halfway into his own asshole, Cas shoots a glare over his shoulder. It’s half exasperation and half discomfort.

“Our parents are out of town.” His voice is a little less composed than his expression feels. “Your brother is at a friend’s. My brothers are at a party. We may not get a chance like this again until we move out, and even then we’ll have roommates and RAs to contend with, so unless the next words out of your mouth are ‘I changed my mind and don’t want to do this anymore,’ shut up and let me get ready.”

He twists his finger to prove the point, which is a poor decision because the only one he’s hurting is himself. It tugs at the delicate skin and he eases up, trying to relax around the penetrating digit. Dean steps closer, still looking torn between concern and arousal; Cas’s next wince, unfortunately, tips it to the former.

“Jesus, Cas. Of course I want to. But I want it to be good for you, not... You’re hurting yourself, baby.”

Keeping his neck craned is too much work on top of what he’s already doing. Cas turns back and lets his forehead drop against the mattress as he grits his teeth and chokes out, “I just need to get used to it,” through the burn that makes pushing his finger farther in ill-advised.

“You need to stop,” Dean counters. His warm hand settles on Cas’s wrist, stilling him. “Just—just listen to me for a second, please? We’ve got all night.”

It takes the edge of panic in Dean’s voice for Cas to realize that maybe he’s a little frantic, too. Taking a deep breath, he slowly pulls his finger free and rolls over to lie on his back against the soft flannel sheets. He just wanted this to be perfect, his present to Dean, and he’s messing it up. He should’ve done this part before, then at least Dean wouldn’t have to see it. But Dean is already here and worried now, so Cas has to work with what he’s got. He can still salvage the night.

“I’m okay,” he says. This time it’s more than just words.

He holds out his hand and Dean looks glad to take it, relieved to join him on the bed. He even reaches for Cas’s other hand and doesn’t seem to care that it’s sticky with lube and was part way in Cas’s ass a second ago. He just holds Cas, their hands tightly clasped and foreheads pressed together.

“Are you?” Dean asks softly.

The lingering tenderness of his hole aside, he is. “Yes, Dean. I’m sorry to have worried you. I just... I had a picture of how I wanted the night to go, and it’s frustrating for it not to be perfect.”

Dean’s laugh isn’t unkind, but it still tickles Cas’s self-consciousness until Dean leans in to kiss him softly.

“Sweetheart,” he says against Cas’s lips, “of course it’s going to be perfect. Doesn’t matter what happens or doesn’t happen tonight. It’s perfect because it’s you and me. That’s all we need.”

Pulling back, Cas levels another glare at Dean, though it’s half-hearted at best. “What I need is to have sex with my boyfriend like we’ve been planning all week. Unless you don’t want to. I don’t need to be soothed like some—some trembling teenage coming of age novel heroine.”

Dean sits up straighter, and now he looks a little grumpy, which isn’t at all what Cas wanted. “It kinda seems like maybe you do,” he says. His voice is tense again. “This isn’t... It doesn’t need to be such a big thing, Cas. I mean, I’m not saying it’s not, just, you know. We’ve done stuff, we’ve had sex even if it wasn’t like this. And it’s good, right? Even if things go wrong sometimes.”

The first time he’d gone down on Dean, Cas tried to take it too far and gagged. But they recovered and worked through it, and Dean’s right, it is good. But Dean’s the experienced one, the one who had partners before Cas, the one who’s had real sex with people. Cas hates feeling like the struggling virgin. Like he’s holding Dean back while he tries to catch up.

So he feels like he has a lot riding on tonight. He’s been ready, or at least thought he was ready, for months, but this is the first and maybe only time they actually have a chance to do anything about it before the summer ends and they start college. He just wants to have sex with his boyfriend, that doesn’t seem like too much to ask for. Except of himself, apparently.

Dean hasn’t stopped giving him the kicked-but-still-protective-puppy look, so Cas has to do something right, and quickly, or risk ruining things even further. He wants to trust in Dean’s sincerity, that Dean’s not put off by his lack of experience and his unsuccessful fumbling around with his uncooperative ass, but the part of him that took three weeks to believe Dean Winchester was actually asking him out won’t let him. He would’ve hoped that part would’ve learned to shut up now that he and Dean have been together for over a year, but it’s still a work in progress.

The best he can do, and what he does, is pretend. Fake it ’til he makes it, so to speak. Even if he still feels the pressure to perform perfectly internally—which, on deeper introspection, might be a bit shrinking virgin of him after all—he can act like it’s all fine. It will be fine, as long as he can pretend it is.

“Right,” he answers finally. “It’s good. It’ll be good.”

He sounds a little stiff, and not in the good way, but it’s an improvement. Not enough of an improvement for Dean to start things up again, though, so Cas takes that task upon himself. He pulls Dean in close and plants a kiss on him that Dean thankfully doesn’t resist.

This, at least, he knows he’s good at. Dean groans and leans into it, tongue pushing into Cas’s mouth until Cas doesn’t have to pretend to be over his nerves anymore. The familiar heat of Dean’s kisses, Dean’s body pressing him down onto the bed, Dean’s hands covering his skin in caresses—these settle him.

When he reaches back to test his finger inside himself again, it goes a little more easily. He’s relaxed, playing with it instead of forcing his way toward a goal. It feels weird, still. Uncomfortable, but not painful.

Then Dean’s hand slips away from him and slips back and down, almost magically wet with more lube. He doesn’t stop kissing Cas, nor does he start opening him up; he teases his finger around Cas’s hole, rubbing softly at the tender ring until the nerves spark instead of pinch.

“Oh,” he gasps against Dean’s lips when it starts to feel good. “Oh, Dean!”

“That’s it, baby. Just like that, see, doesn’t need to hurt.”

Distracting Cas from a response, Dean sucks his way down the line of Cas’s neck, scrapes his teeth lightly over blood-hot flesh, and nudges the tip of his finger alongside Cas’s. He doesn’t even do much when it’s there, wiggling it in little twitches that remind Cas of its presence without the tug of a stretch. His thumb takes up the job of stroking around the rim, touches that soothe and entice in equal measure so that Cas can lose himself in it.

Cas doesn’t even realize he’s hard again until Dean moves just so and their dicks bump together. Stunned by how intense that minor contact feels, he bucks up in search of more, but he doesn’t find it. Dean pulls his hips back with a chuckle to deny him that friction. But the way Cas’s movement makes him tighten around the fingers—finger and fingertip, still—inside him is its own brand new sensation and he freezes with it.

Dean’s finger pushes in further at the same time as he drops his head to suck Cas’s nipple between his lips. The soft heat of his mouth makes Cas melt, relaxing without thought, which in turn lets the digit slip in significantly more easily. Then another fingertip taps against Cas’s knuckle and Dean separates from Cas’s chest long enough to murmur, “Let me.”

Pulling his finger out is strange; he feels oddly open around just Dean’s single finger inside him, and his ass seems slightly reluctant to let him go at the very end. But as soon as he’s out, Dean’s refilling the space, rocking slowly into Cas with two fingers. He curves them in a way Cas never would have been able to with his own poorly angled pointer finger and Cas’s gasp comes out much more like a scream with the way that Dean’s touch shocks his whole nervous system.

“There it is. You like that, sweetheart, that feel good?”

Dean doesn’t press over his prostate again as he waits for an answer, though he does work his fingers out and in a little at a time, starting to spread them every so often. It’s a good thing, because Cas doesn’t think he’d be able to form a coherent thought at all with Dean doing that again.

Even as it is, it takes him a few shuddering breaths to gather himself enough to say, “Yes. That feels—good. Very good.”

Pushing up for another deep kiss, Dean grins at him. “Then you’re gonna fucking love this,” he says, then slides down Cas’s body and takes Cas’s dick halfway into his mouth with no other warning. Only his free hand wrapping around the base keeps Cas from accidentally choking him as he reflexively humps up into the feeling.

Cas would apologize, but he’s far too overwhelmed by the twin sensations of Dean’s tongue circling all around his dick and Dean’s fingers rubbing insistently at his prostate. It’s right at the edge of too intense, nearly enough to drive Cas past pleasure into insanity. But no matter how close to the line Dean takes him, no matter how long he rides next to the boundary, it never crosses over.

At some point—Cas has lost all sense of time, it could be seconds or minutes or years—Dean has another finger inside him and a hand fondling his balls and most of Cas’s dick down his throat, and that’s all Cas can take. His hands are in Dean’s hair and Dean’s name is shaking out of his lungs with every gasp. He comes before he knows it’s happening, before he can warn Dean, but Dean just swallows it down without missing a beat.

Cas is shattered in the wake of it. His body feels remade, exhausted from being sculpted beneath Dean’s hands but glowing with sated energy. He’s no stranger to orgasms, with or without Dean. With is always more intense, but nothing they’ve done before has left him feeling quite so charged.

So when Dean sits up and starts to jack off next to Cas’s leg, Cas props himself up on one elbow and grabs Dean’s hand to stop him. Dean looks down in confusion, mouth open on a question.

Before he can get it out, Cas says, “Get the condom.”

Dean blinks at him, but his surprise is overshadowed by hunger. Dark, wide eyes rove over Cas’s body as he inches hopefully closer. “Are you sure? It’s probably going to feel even weirder now that you’ve come. We can wait.”

His earlier ire tries to rise up at Dean’s coddling, but he’s too content for it to take hold. Dean’s sweet caretaking is part of who he is, and part of why Cas liked him to begin with. He can allow Dean to look after him if that makes Dean happy, but he’s no less certain now than he was before they started.

“I’m sure. I want you inside me, Dean. I want you—I want us to have this. Get the condom.”

Dean doesn’t have to be told a third time. He scrambles over to the nightstand and grabs a condom from the box, slipping a few times before he manages to tear it open. Part of Cas wishes he could help Dean roll it on, but he’s still feeling too lax for that kind of fine motor control. So he settles for watching, this time. it doesn’t take long enough for him to intervene, anyway.

A palmful of lube later, Dean kneels between Cas’s thighs and takes a deep breath. Cas lifts a leg up around Dean’s waist; Dean’s hand drifts down and his finger touches the edge of Cas’s hole. It slips inside without fuss and Cas shivers, which makes him clench around Dean.

“Oh, fuck. I gotta—tell me I can—”

Dean lines himself up before his finger is even all the way out, pushes in as soon as Cas says, “Yes, yes, do it.”

It’s a stretch, more than Dean’s fingers were, but smoother than bony knuckles. Uncomfortable, definitely not as pleasurable as when Dean was sucking him off and playing with his prostate, but it’s not painful. And the wonder on Dean’s face, the completion Cas feels at having his boyfriend’s dick slowly rocking into him, each tiny thrust deeper than the last, makes the experience an amazing one.

Dean’s holding back, trying to be gentle, but even so Cas can’t help that his groan isn’t entirely blissful as Dean makes the final push to bury himself all the way inside. Dean doesn’t start fucking him straight away; he stays mostly in place and folds over instead, pressing his body down against Cas’s and kissing him slow and sweet.

“You feel so good, baby,” he tells Cas once Cas’s breathing has had time to even out as he adjusted to the dick in him, then speed up again from the heat of Dean’s mouth on his. “Fuck, you’re amazing. How does it feel?”

“Full,” is Cas’s first instinctive response, because it’s the truth. He’s filled up in a way he never has been before, and while not unpleasant, it’s certainly weird.

But it’s not so different from Dean’s fingers, and that went from strange to extraordinary pretty quickly, so his next answer is, “Exciting. I want to feel you, Dean.”

“Yeah,” Dean breathes into him. “Yeah, I’ll let you feel me. But it’s—it ain’t gonna be for that long, baby, not with how good this is.”

“I’m not doing anything,” Cas protests. He knows what Dean means, though. Dean isn’t moving in him, either, but Cas would probably be ready to come at a touch if he hadn’t just done it.

He’s a horny, barely devirginized eighteen-year-old, so his dick makes a decent effort at getting involved again when Dean draws out over his prostate and slides back in along the same path. Maybe with enough time he could get it up, but Dean was right. Experience, condom, and tenderness all notwithstanding, he’s fewer than a dozen thrusts in, moaning Cas’s name with each one, when he shudders and gasps.

“Oh, fuck. Cas, fuck, Cas.”

Cas arches up and Dean curves down and they meet in the middle for an open-mouthed kiss that’s more of a sloppy smear of lips. Dean’s in him and over him and on him, and he’s never felt so much a part of something greater than himself. He almost tells Dean, but he’s been working up to a confession even longer than he’s been planning to have sex with Dean. He doesn’t want his first ‘I love you’ to come in the wake of coming.

Dean rocks into him a last, shuddering time and stills. The extrication is back to being awkward, a bit too tender, but then Dean finishes tying off the condom and wraps Cas up in his arms. They lie together on top of Cas’s bed, basking in each other.

“Was that okay?” Dean asks against the curve of Cas’s shoulder. “Sorry I couldn’t last, couldn’t make it better for you—”

Cas twists around to silence him with a kiss. Dean’s insecurities don’t show themselves often, and are always understated when they do, so Cas sometimes forgets enough to be surprised by them. But they’re there, even when Dean should have nothing to worry about.

“It was amazing, Dean. It was good, you were so good.”

“Yeah?” Dean grins, charm showing through the shyness. “Good enough you might wanna do it again sometime?”

Rolling onto his back and dragging a surprised Dean with him, Cas returns the smile. “You know, we have the house to ourselves for at least another three hours.”


End file.
